ITunes won't play some CD's I upload

Question

I have an old 40GB iPod- I think it is the 4th generation (right before iPods with color screens came out). Every once in a while, I upload a CD that won't play in iTunes, and I don't know why. I have deleted the CD's from iTunes and uploaded them again, and they still won't play. I have updated my version of iTunes and done the whole process again, and it still won't work.
I was uploading my Dropkick Murphys CD's, and found 4 of the CD's that won't work:
Do or Die
Live on St. Patrick's Day
Tessie (EP)
Singles Collection Volume 2
All of these are uploaded from original, store-bought CD's straight to iTunes. I have not synced the iPod to my iTunes library lately, because my old computer died and I don't want to lose the several thousand songs that are on my iPod. (Why won't iPod let you download from your iPod to a new computer? Aaarrrrgh!)
When I click on the first song on that CD in my iTunes library, the little "speaker" icon next to the track just seems to fall down the list of songs. Nothing plays, and it only takes about a second for the speaker icon to fall from one tune to the next. When it reaches the next CD, it starts playing normally again.
I've also noticed that it shows "0:00:00" for the time remaining AND the time elapsed when iTunes tries to play the songs I'm having trouble with. The track length shows up as some ridiculous number, like "789:57:13."
How can I fix this so that I can enjoy all of my music?
Message was edited by: Rory Gentry
Message was edited by: Rory Gentry
Message was edited by: Rory Gentry

Answer 1

I'm not completely sure HOW it happened, but I managed to get 90% of my songs transferred from my iPod to my computer, iTunes updated, and now ALL of that music is on my iPod again.
Floola worked well, but it would be nice if their website had some better instructions. After getting music transferred from my iPod to Floola, I copied everything in Floola to a new folder on my computer and closed Floola. Next, I opened iTunes and the folder I had copied the music to. I minimized them so that both cold be seen on the screen at the same time.
When I started moving music from the folder to iTunes in small batches (about 50), I could more easily identify which songs were causing the error that said some titles were too long. When I encountered that error, I moved a smaller portion of that batch of songs until I found the exact problem. I put the "problem" songs into another folder to deal with later. (It turns out that those songs were all limited to 3 or 4 albums, which I will re-load manually from the CD.)
Once I was done copying all of the songs from the folder to iTunes, and the problem songs had been moved away to a new folder, I thought I was done. I shut down everything, and restarted my computer. I opened iTunes and the music folder again, and this time selected everything in the music folder (not just batches of 50). I dragged the entire list (5000 songs) to iTunes AGAIN, and my music library grew once more. I'm not sure why this happened since all of the music had been moved once before, but I'm glad I did it. I gained another 500 songs!
After the last copy session from the folder to iTunes, I shut everything down once again. I started iTunes, sorted a few playlists, and plugged in my iPod. It updated perfectly.
*+THANKS TO EVERYONE HERE WHO HELPED! I would still be stuck without all of your expertise and advice!+*